Expect Everything to be Unexpected

How does it feel to do a startup?

Imagine Chuck Palahniuk, M. Night Shyamalan, and Kurt Vonnegut got together and wrote a book. Your startup experience will still be more fucked up.

(This is an interlude of The Epic Guide to Bootstrapping a SaaS Startup — By Yourself.)

You’re ragged. You’re spent. You’re running out of time. You can’t seem to find a way out. Every success seems to bring more failure. Just around the corner is ruin and destruction. Things that should work don’t. Things that shouldn’t work do. And best of all — you have no idea why.

You’re running out of runway. How should you spend your last cash reserve?

A. Hire an unknown freelancer to build out that feature you think would be game changing

B. Take out more ads, even though they haven’t been bringing any new customers

C. Admit you suck at marketing and sales and hire an agency or a sales rep

D. Throw the towel in, pocket whatever you can, and try to find some contract work ASAP

Welcome to Startup Club. Where every step of the way is about as obvious as the choices given to you in a Choose Your Own Adventure book.

At least they only limit you to 20 ways to fail.

What to expect when dealing with the unexpected

Building a SaaS startup from scratch is unlike anything else you’ve ever experienced.

If you graduated from some type of school (be it high school or college), have held a job in the real world, and are a generally responsible person, you are completely unprepared for what awaits you.

The reason for this is that there are clear, known pathways to success in all of those endeavors. If you memorize the formula and follow the routines, you succeed.

School? Pay attention in class, take notes, do your homework, study. It’s not that hard. There are known right and known wrong answers to every fact you are asked to regurgitate.

Work? Show up, do what your manager asks you to do. If you don’t know something, read up on it. Get work done by the time it’s due. Make sure whatever you deliver meets whatever guidelines were given to you. If your manager forgot to tell you to do something, it’s not your fault if it didn’t get done.

Responsible person? Don’t spend more than you make. Pay your bills on time. Clean up after yourself. Do what you’ve committed to doing.

Pretty simple, right?

Do these things and you’re a shining example of success to everyone around you. It’s honestly not hard to be successful when playing by those rules.

But building your own business (let alone a SaaS startup) is completely different.

Those rules don’t apply.

Everything you thought you knew about being “successful” won’t help you here.

And this is why so many people ultimately fail at building a startup.

They’re playing by the wrong set of rules.

They don’t know that in fact, there are no rules to success in Startup Land.

Just another day in Startup Land.

What could go wrong?


Let’s take just a few examples from my experiences while building Tamboo:

  1. I did some early one-on-one customer development and got a lot of excitement and interest from the people I reached out to. I got roughly 20 people to say “Heck Yes!” to trying out Tamboo as part of a beta program. When the time came, only one of those people went forward with the beta. No one else even responded to follow up emails (even though we had been going back and forth).
  2. I collected roughly 50 email addresses from a landing page. I was 100% clear about what Tamboo was going to be, what it could be used for, and that by giving me your email address, I’d let you know when it was avilable for use and you’d get to use it for free for three months. When launch time came a short while later, none of them signed up for the service. And better yet, no one responded to inquiries about why they weren’t signing up. Even after having had prior email exchanges with them. Lovely.
  3. I did a number of Facebook and Twitter ad campaigns that yielded absolutely zero signups. To this day, I honestly don’t know if it was my targeting, placement, or messaging on those ads that didn’t work. (I eventually got ads working, but there are still times when the results trend towards atrocious.)
  4. I bumped up my marketing efforts and got a number of signups. Only problem? None of them were installing the JavaScript snippet on their website that Tamboo needs to do its magic. (Multiple) emails to those people went completely ignored.
  5. I eventually got people signing up for the service, installing the JavaScript snippet (yes!), and then — nothing. After the initial setup, they never logged back into Tamboo again. And you guessed it — emails asking why went completely ignored.
  6. Upping my social media marketing, I was getting a ton of retweets, likes, follows, etc. — on articles that nobody ever bothered to click on or read. (This is still probably my favorite WTF. What are they even thinking? “Yeah, that’s a great headline!” Retweet! Like! Seriously.)
  7. Let’s not forget the click fraud. People clicking on ads and then bouncing from the page in 0.067 seconds. (As an aside, using Tamboo on Tamboo’s marketing page has been an invaluable learning experience.)
  8. Having people get excited by the service, sign up for it, use it, but then say that it would really need to do X before they’d be willing to pay for it.
  9. Having people want to use the service for something it wasn’t intended for and demanding to know how they could get it to function in that use case.
  10. Oh, and let’s not forget all those blog posts and content marketing pieces that I spent 12 hours a piece on that I thought were going to be grand slams that everybody ignored.

Does that help paint a rosy picture for you?

Oh, and that’s just when you’re starting out. It gets more fun from there.

That’s one of the reasons most developers trying to bootstrap their startup run back to writing code — marketing and sales are nasty, ugly, disheartening experiences that you’ve got to work at before you see any kind of results. By contrast, programming gives you instant feedback, gratification, and a sense of control.

Learn to love the suck.

Why, yes. Yes I do.

The trick is to treat everything like a giant game.

It’s a giant puzzle like that game Labyrinth (or maybe even an IRL version of the movie).

Most people treat it too seriously and get it wrong. Seriously wrong.

You’re most likely coming from a structured environment where the expectation is that every move you make must result in success. Any move that does not result in success means that you are doing something horrifically wrong that must be corrected. It means that you are no good. It means that you are a failure. It means that you’re fucking up. It means that you’re on the road to ruin.

That kind of attitude will end your startup game before you even get past level 1.

Instead, you must learn to laugh at failure. You need to learn how to accept that “this didn’t work” without thinking any less of yourself.

You have to disassociate yourself. Your worth is not determined by how well you play this game. Your worth just needs to be determined by the fact that you are playing this game. And that you’re going to calmly figure out what your next move should be, regardless of how many failed moves you’ve played up until now.

Think of it this way.

You don’t just sit down for the first time at chess against someone who has been playing for years and expect to win. You don’t play once, lose, and then give up any hope of ever being good at chess.

You don’t really understand the game, let alone the strategy. You have to accept that. You have to walk into that game thinking “I’m going to do this, I’ll try my best, but my goal here is to learn something about how to get better for the next game.”

You do that same thing with every game that you play until you get good.

You don’t get worked up, you don’t expect to win. You don’t expect anything to go the way that you would like it to, except that you’ll learn something that will help you improve. You don’t throw your hands up and quit.

And most definitely, you don’t make big bets on the outcome of the game. Expect that you’re going to lose for a long time before you start to win. Bet accordingly.

That’s how you play the startup game.

You can’t predict people.

Nothing but love for all the internet denizens out there.

Put the book down.

No, seriously. Put it down.

Now go grab some tape.

And wrap that tape around that fucker until you can’t open it again.

I don’t care if you’re working your way through Zero to One, The Lean Startup, Running Lean, Rework, Good to Great, or whatever other “must-read” business book they’re peddling nowadays.

They aren’t going to help you.

In fact, they’re hurting you. Trust me on this. I’ve spent way too much time reading books instead of doing things. Years. A decade. Don’t make the same mistake I did.

The truth is, the minute you commit to doing your startup, nothing in any of those books is going to hold any relevance. They will offer you no help. NONE.

That’s because those books were written by people based on their experiences. Not yours.

Their experiences will not help you get off the ground.

Trust me on this.

Want to try a fun exercise? Try to copy a competitor’s marketing campaign — word for word, image for image, placement for placement. See what kind of results you get.

You’d think that you’d be able to score taking an approach like that. But you won’t.

Because (and this is super important) you can’t reproduce other people’s successes.

The only explanation I have for this is that you can’t predict people.

The people that helped that someone you look up to become successful — by becoming customers, spreading their content, etc. — will not respond the same way to you.

First of all, good luck reaching those exact people.

Second of all, they’ve already seen it. So they’re not going to go nuts over you.

Third, that person you look up to found a way to resonate with those people at a time and a place and in a way that is now in the past.

You have to find your own way to resonate with people. At time and a place, and in a way that works for them.

But the truth is that you just won’t know.

You can’t predict people.

You can’t predict what they’re going to do after they sign up for your launch list.

You can’t predict what they’ll do when they see your ad.

You can’t predict what they’ll do when they sign up for your service.

You can’t predict what they’ll do.


(Important bit coming up here.)

Because people will do whatever they want to do — regardless of what you want them to do.

And that’s why you should expect that every step of the way will be unpredictable.

Because your success is based on what people choose to do with what you’re putting out there.

And you can’t predict what people will do.

You can only try things, see what happens, and try some other things.

Over and over again, until something magical happens. And then you’ll sit there and wonder why the hell that worked when nothing else did, and how you can reproduce that success again.

Welcome to Startup Land.